- Actor-Shared Background:
- While Robert De Niro is most well known for his Italian-American gangster roles and is himself Italian-American, he actually has more Irish ancestry than Italian, being only a quarter Italian and about 30% Irish (his father was half-Irish, and his mother had some as well). Previously, he had played the Irish-American gangster Jimmy Conway for Scorsese in Goodfellas. However, in real life, Frank Sheeran's mother was of Swedish descent, and as a result he had blue eyes and sandy hair.
- Dascha Polanco plays Frank's nurse in one of his final scenes and was training to become a nurse before she decided to try acting.
- All-Star Cast: The major players are Robert De Niro, Al Pacino and Joe Pesci, with supporting performances by Harvey Keitel, Ray Romano, Jesse Plemons, Bobby Cannavale and Anna Paquin as well as a large cast of prolific character actors.
- Awesome, Dear Boy: Anna Paquin really wanted to work with Martin Scorsese, no matter how small the role she got.
- Cast the Expert: The two Catholic priests who appear in the film are both real priests (though one of them has since left the priesthood).
- Channel Hop: Paramount dropped the film over the rising budget, allowing Netflix to swoop in and pick it up.
- Dawson Casting: 35-year old Anna Paquin plays Peggy as a young adult up to middle-aged.
- Fake American: Brit Stephen Graham plays another American gangster after perfecting the art in Boardwalk Empire and Public Enemies. Jack Huston, also British, plays Bobby Kennedy.
- Irony as She Is Cast: Jimmy Hoffa (who was German-American and Irish-American in real life) is shown to be prejudiced against Italians/Italian-Americans and often hurls anti-Italian slurs during conversations. He is played by the very Italian-American Al Pacino.
- Playing Against Type:
- As Russell Bufalino, Joe Pesci plays a cautious and restrained crime lord, far from the hot-tempered mooks he's more well known for.
- Comedian Ray Romano plays an Amoral Attorney totally straight.
- In the Latin American Spanish dub, Armando Coria as the titular character is this, as, while this is not the first time he has voiced reprensive or evil characters before, he is normally type-casted on voicing heroic roles or the Nice Guy, like Hikaru Matsuyama, Spider-Man or Willykit.
- Production Posse: Director Martin Scorsese, screenwriter Steve Zaillain, editor Thelma Schoonmaker, costume designer Sandy Powell, and stars Robert De Niro, Joe Pesci, Harvey Keitel and Bobby Cannavale have all worked together in the past.
- Role Reprise: In the Italian dub of the movie Giancarlo Giannini dubs Al Pacino's Jimmy Hoffa, and in the past he already dubbed Jack Nicholson's portrayal in Hoffa.
- Saved from Development Hell: Martin Scorsese has been thinking about directing the film since about 2007. Netflix eventually ensured it got made. The project was thought of as too costly for its niche genre by the traditional movie studios Scorsese previously tried to sell it to.
- Scully Box: Robert De Niro is an inch taller than Al Pacino, but to make Frank Sheeran much bigger than Jimmy Hoffa, impressive heels were worn.
- Those Two Actors: This is the fourth film featuring both De Niro and Pacino (after The Godfather Part II, Heat and Righteous Kill),note and the sixth film to feature De Niro and Pesci (after Raging Bull, Once Upon a Time in America, Goodfellas, A Bronx Tale and Casino), though Pesci had a small appearance in De Niro's The Good Shepherd. This was also the ninth film featuring De Niro and Harvey Keitel (after Mean Streets, Taxi Driver, Falling In Love, Cop Land, The Bridges of San Luis Rey, Arthur and the Invisibles, Little Fockers, and The Comedian.
- Throw It In!: Ad-libbing was apparently encouraged in the set to an extent. Most notably, Tony Pro suddenly hurling away Hoffa's tray of ice cream was a bit of improv on Stephen Graham's part. Al Pacino's stunned reaction to it was genuine.
- What Could Have Been:
- Sacha Baron Cohen was to have a role in the movie, but he declined due to filming his series Who Is America?.
- As a back-up plan in case Joe Pesci refused to come out of retirement to play Russell Bufalino, Scorsese intended to have De Niro play Russell and cast either Liam Neeson or Pierce Brosnan as Sheeran. Neeson actually bears a closer physical resemblance to the real Sheeran than De Niro (which becomes funnier because he's Irish and the same height as Frank Sheeran).
- Mickey Rourke claimed in an interview that Martin Scorsese had asked him to appear in the movie, but he refused due to an ongoing feud between himself and De Niro that began during the production of Angel Heart. However multiple sources have claimed that wasn't true and Mickey was never offered a role.
- Ray Liotta expressed interest in playing a role, possibly even reprising his role as Henry Hill from Goodfellas, but it ultimately fell through.
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